George Jeremy 386, more commonly known as Weirdo386, is Lollipop386's weird brother. Weirdo386 was born on April 1, 2000 in Club Penguin Island. He always talks in bad grammar, making Director Benny angry. Weirdo is friends with Explorer 767. He has had several jobs over the years, such as a TV actor and a pizza chef. However, he often gets fired due to his incompetence. He owns a pet cucumber named Joe. He always wears a rainbow propeller cap over his bald head. He also always wears the color light blue. He used to call himself "683Popillol" because he considered himself the opposite of Lollipop. In 2016, he changed his nickname to "Weirdo386", because he didn't want to be confused with the unrelated criminal Popillol B. Waddles, and because everyone called him "weirdo" already.

Matthew Lolz 386 (better known by his stage name, DJ386) is a mildly successful DJ. He was born on July 20, 1997 in Club Penguin Island, making him the oldest of the Lollipop Brothers. When he was five years old, Matthew loved music and wanted to be a musician when he grew up. In 2007, he specifically decided that he was going to be a DJ. Being born and raised on Club Penguin Island, he was a huge fan of the immense musical talent around his hometown. One of his favorite bands at the time (and to this day) was the Penguin Band. When DJ3K was released in the Night Club in 2008, he started going there every day after school to play it. Although he wasn't very good at first, he learned over time and became great at it. By the end of the year, the Night Club hired him as an official DJ — his dream came true when he was only 11! It was then that everyone started calling him DJ386, a stage name and nickname he retains to this day. He wrote his first song in 2009, and later on bought a black puffle who he named DJ Fireball. Since then he has taught the puffle everything he knows about DJing, and because of it they are the perfect duo. He has now written over 40 songs.

Petey Francis 386 (commonly known as Party386) is a fun penguin who loves anything related to parties. He owns many party hats, since he is a collector of sorts. In his total collection, he has about 3,000 party hats. In 2005, he gave a beta hat to his brother Prankster386. Due to his fondness of party hats, Party is also a key contributor for the International Party Hat Museum on Shops Island, loaning or giving many of the hats from his private collection to the museum, and also donating countless dollars and hours to the cause. Party also works for the Penguin Color Painting Agency.

John Jones 386 (also known as Prankster386, formerly known as Repeater338866) is a prankster and stand-up comedian. He was born in 1999. He always wears his Beta Hat, which was given to him by Party386. He is good friends with Rookie. He used to be known as Repeater338866, because he repeated things that other people said, and couldn't control it. Strangely, he only repeated some things, but not everything. He also said everything twice. It was unknown why he repeated what other penguins say, but it was rumoured that it was because of the Beta Hat.

In May 2018, Gamer Gadget made him a device that alters his brainwaves, stopping him from repeating anything. The device is built into his Beta Hat, so he must wear it at all times. Ever since he stopped repeating, he's become much more talkative, and even hired as a motivational speaker. Mostly, he just does stand-up comedy, and does pranks and practical jokes.

Calvin Peter 386 (also known as Clumsy386) is, as you can tell by his nickname, very clumsy. He has been known to break almost everything he touches. He was born in 1998. He is a genius, but unfortunately, his clumsiness keeps him from utilizing his potential. He went to medical school and got a PhD, and became a doctor in 2011. He was fired on his first day, due to causing a terrible accident in the operating room and nearly destroying the hospital. He now owns his own shop, selling fine china, expensive jewelry, and glass vases. He is always seen wearing a bandage on his head.

Jordan Alexander 386 (also known as Annoying386) is the most annoying penguin of all time. He was born in 2001, making him the youngest of the Lollipop Brothers. The only person who doesn't find him annoying is his good friend Winston. Even Mabel X and Goody386 think he's annoying, but they're too kind to admit it. The cause of his annoyingness is that before he hatched, his egg was dropped off a cliff and frozen in ice for a month. He is an aspiring musician and singer, but his songs have caused peoples' brains to explode — literally. He is one of the few people who enjoy WHAT?!?, and he dedicates at least five hours a day to watching it on repeat. He was one of the main characters on the TV show Lollipop's Adventures, before it got cancelled and replaced by his own show, Sing-Along Time with Annoying386. His show airs daily from 2:00 AM to 3:30 PM.

Timothy Craig 386 (also known as Goody386) is the nicest of the Lollipop Brothers. He was born in 2000. He always uses his manners and is a member of Goody Two-Shoes. He is always optimistic, and has never been seen angry or untruthful. He always addresses everyone by their full name, unless asked not to. He is best friends with Mabel X, and doesn't mind Mabel (who he often misnames "Marble"), but he is severely annoyed by Annoying386. However, he would never admit it. He wears glasses, and without them, he can't see two inches in front of his face. He is smart in terms of math and science, but not so bright in terms of logic. He usually doesn't realize anything unless specifically told to him, and doesn't understand sarcasm. Coincidentally, he always seems to be missing when a bank robbery or crime occurs on the island.